


A Date to Remember

by dickspeightjrs



Category: Supernatural
Genre: Alternate Universe - Reality Show, Angst, Angst with a Happy Ending, Emotional Hurt/Comfort, First Dates, Fluff, Fluff and Angst, Heartbroken Castiel (Supernatural), Hurt/Comfort, M/M, Panic Attacks, Reality TV, Reunions, Sad Castiel (Supernatural), Self-Doubt, True Love
Language: English
Status: Completed
Published: 2021-01-28
Updated: 2021-01-28
Packaged: 2021-03-14 16:41:19
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,667
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29049330
Author URL: https://archiveofourown.org/users/dickspeightjrs/pseuds/dickspeightjrs
Summary: Living a miserably single life had finally got old for Castiel. After a few failed dates, he’d decided he had nothing to lose by signing up to the First Dates show he’d seen on Netflix.
Relationships: Castiel & Anna Milton, Castiel/Dean Winchester
Comments: 5
Kudos: 105





	A Date to Remember

**Author's Note:**

> Based on the reality TV show 'First Dates'.

Castiel traces the condensation on his glass. He’s barely touched the beer since the barman set it down in front of him. To say he’s second guessing his decision to do this would be an understatement.

Living a miserably single life had finally got old for Castiel. After a few failed dates, he’d decided he had nothing to lose by signing up to the _First Dates_ show he’d seen on Netflix.

However, he is starting to regret it. His date hasn’t even arrived yet and he’s already dreading the evening. The awkwardness of introducing yourself, trying to find the bits of your life what would interest another person and not scare them off. Trying to fake interest as someone drones on about their collection of antique globes. That had been a date that Castiel certainly never wanted to repeat.

And then there’s the added pressure of it all being recorded for television. Regardless of how the evening goes, his brother, Gabriel, is bound to use the footage as an endless source of teasing and amusement.

“You alright, man?” The bartender, Benny, according to his name badge, interrupts Castiel’s thoughts.

Castiel sighs and finally takes a sip of his beer. “Yes, I suppose I’m just nervous.”

“Ah, I wouldn’t worry about it. Everyone here is nervous at the start.” Benny shrugs. Well, except the ones who are pretty, and they know it,” he chuckles. “And I’ll be honest with ya,” he says, leaning on the bar closer to Castiel, “very few of the couples who go on the show end up together anyway. Don’t stress. Enjoy the evening. If nothing else, it’ll be a story to tell.”

Castiel knows the cameras are rolling and suspects that’s not something Benny should admit to but he’s grateful for the advice nonetheless. It does help settle his nerves a little. This evening probably won’t go anywhere, and he’ll return home to his cat just the same person as he had been this morning.

Castiel nods to Benny and finishes off his beer in one final sweep. He hands his empty bottle to Benny and asks for another.

Benny passes over another beer, placing it on the counter in front of Castiel.

Castiel is about to take a sip when something catches Benny’s eye behind him. Benny nods slightly in the direction of the door. “Don’t look now but I think your man has arrived.”

Nerves come flooding back and Castiel finds himself frozen facing Benny.

“Well, man, I know you’re nervous but I think you’re in for a good night. Your date is certainly a looker.”

Castiel swallows. He still hasn’t got the strength to turn around. This time Benny’s words don’t calm him. Knowing that the person he’s about to meet is attractive, and that is coming from Benny who isn’t so bad looking himself, Castiel feels his heart rate pick up.

Benny walks away as Castiel senses a presence behind him.

“Castiel,” the voice of the maître d’ comes from behind him, “this is your date for the evening.”

Castiel turns.

And the breath leaves his body.

“Dean?”

“Cas?” Comes the equally as breathless response.

The maître d’ slinks away with a look on his face like he new exactly what was going to happen.

Benny has moved away too. Castiel can see him in the corner of his eye pretending to clean glasses while watching the exchange between Dean and Castiel.

Castiel lets himself take in the appearance of the man in front of him. The man he never thought he’d see again.

Dean Winchester.

And suddenly Castiel feels himself being taken back eight years.

It was a classic college romance. Dean and Castiel were paired together in dorm allocations and became instant friends. Castiel never would have seen himself forming a friendship with someone as out-going as Dean. But the funny thing about sharing a room with someone, you soon learn the things they’d like to keep hidden. Things that could warm them to somebody like Castiel.

For Dean, it was that he was homesick for his family. He’d decided to attend college thousands of miles away from his home state, and his family.

Castiel couldn’t relate. He’d also moved away from his family but it was a decision he could never regret. He couldn’t wait to get rid of his parents and leave his small town behind. His siblings had all already left and were also not returning.

It wasn’t long before roommates turned into a relationship.

From there it seemed to everyone, including Dean and Castiel themselves, that everything was like a fairy-tale They had their ups and downs but always came through together.

By the time graduation rolled around, they were set to be together forever. They had plans to move in together properly after Castiel accepted his dream job, which was rarely offered to anyone just out of college.

But this particular fairy-tale didn’t have a happy ending.

A couple of weeks before graduation, Dean’s mom passed away suddenly.

Despite Castiel doing all he could to console his boyfriend, after Dean returned from his mother’s funeral, he told Castiel he needed to move back home to Kansas to help his dad and younger brother. His dad had fallen to pieces without his wife, and his brother was about to graduate from high school. They needed someone to keep them afloat.

They’d argued so much that night.

Castiel had understood Dean’s need to be with his family and offered to go with him. Dean flipped out and told Castiel that there was no way he was going to be the reason Castiel didn’t follow through with what he’d worked so hard for. That he wasn’t worth Castiel throwing away his life for. Nothing frustrated Castiel more than Dean thinking he wasn’t good enough.

The argument lasted for hours until, eventually, in the calmness of the early hours, they relaxed. Castiel knew the real reason for the argument was that they were both terrified for a future without the other in it.

With a final aching kiss, they parted that night. Each leaving with a piece of the other.

And now, here is Dean, stood in front of Castiel. Looking just as heart-breakingly beautiful as he did the last time Castiel saw him. Even more so, if it’s possible. The years in Kansas have clearly been good to Dean.

Castiel realises he’s probably been staring at Dean a little and he’s painfully aware of the fact there’s probably cameras hidden everywhere recording the blood draining from his face. He clears his throat self-consciously and finally greets Dean with a small, “hi.”

Dean seems to snap out of his own shock and replies with an equally as soft, “hey, Cas.”

Neither of them makes a move, still lost in taking each other in, not quite believing that this is actually happening.

Luckily, they’re saved by the maître d’ returning. “Gentlemen, your table is ready. If you’d like to follow me?”

Dean and Castiel follow the man silently and thank him when they arrive at their table. Soon enough they’re left alone once again.

There’s so much Castiel wants to say and yet he can’t find where to start.

But Dean rescues him by breaking the tension with a soft smile.

And just like that Castiel feels himself smile back, and internally shakes his head at himself. This is Dean. There’s no need for him to be nervous. Regardless of the way things ended between them, Castiel has never harboured anything but fondness for Dean in the years they’ve been apart.

Dean opens his mouth to speak but he’s interrupted by a waiter appearing at the table.

Castiel resists the urge to roll his eyes. It’s not the waiter’s fault, he’s only doing his job. And, up until a few moments ago, Castiel probably would have thanked the man from breaking the tension.

They place their drink orders. Castiel smiles when Dean orders his favourite beer – eight years may have passed but Dean doesn’t seem to have changed all that much.

“So, Cas,” Dean finally speaks once the waiter leaves, “did you sign yourself up for this,” he gestures around at the artificial bar and restaurant set for the show, “or did you get dragged into it by a friend like me?”

Castiel chuckles lightly, “I’m embarrassed to admit that I signed myself up for this. I have no one to blame but myself.”

Dean laughs out loud. His laugh distracting some of their fellow patrons on the tables nearby. Castiel has missed that laugh. The way Dean throws his head back in overwhelmed joy was always one of Castiel’s favourite things about the man. And it still is, Castiel supposes.

“I’ll try not to be too offended by that.” Dean chuckles, amusement clear on his face.

Castiel frowns and realisation dawns on him, “I’m sorry! I didn’t mean it in a bad way!”

Dean smiles again, “don’t worry about it, man. I know what you meant. I’m just teasing you.”

Castiel rolls his eyes in mock annoyance.

They fill the next few minutes with only small talk. As if they’re two college friends catching up after a long time apart, not two people who were so in love they thought they were invincible and that the storms of life couldn’t touch them. They continue to skate around anything to do with the last night they saw each other. They don’t even mention their families. Mostly just their jobs and friends.

Honestly, it does feel good to hear about Dean’s life since college. Despite the circumstances of his return to his hometown, Dean seems to be happy. Even through small talk alone Castiel can tell that he is the same Dean he’d loved all those years ago. He’s learned some life lessons, as has Castiel, but he is still the same person at his core. It’s as if his soul is beaming out to Castiel.

It’s during Dean telling a story about his friend Charlie introducing him to LARPing that Castiel feels it him solidly in the chest.

He’s still completely, unbelievably in love with the man in front of him.

The realisation leaves him a little breathless and he can feel his heart start to pound against his ribcage. Suddenly feeling as if everyone is watching him and ignoring him all at once, Castiel stands from his chair. He knows he’s cutting Dean off mid-story and seeing the look of concern on the man’s face makes Castiel want to flee.

So he does.

“Sorry, excuse me, I need to go to the bathroom.”

Not leaving a second to register Dean’s response, Castiel hurries in the direction of the toilets. He’s painfully aware of cameras set up along the walkway to the bathrooms, he just hopes he moves past quick enough that they won’t be able to see him easily.

Once inside the bathroom, he flings himself into a stall and slams the door behind him. Perching on the closed toilet lid, he tries to focus and keep his breathing under control.

After a few moments, he feels the tension leak from his body. He reaches into his pocket for his phone and dials the only person who could help right now (other than the one sat in the next room).

“Hey Cas! I thought you were meant to be on that date tonight?” Anna’s voice picks up almost immediately. Thank God for his sister being attached to her phone.

“Hello, Anna. I am on the date. I’m currently in the bathroom after having what was probably a panic attack.” Castiel replies calmly, trying to keep his breathing steady.

“What happened? Is the guy an asshole? Do you need me to come get you? I don’t care if it’s for some TV show, I’ll come right down there and –“

“No, Anna, it’s not that.” Castiel interrupts. “It’s- well, it’s-“ he feels tears start to build in his eyes. “It’s Dean.” He chokes, letting the sobs break through his body.

“Oh Cas, I thought we’d settled this years ago. Dean may always be special to you but you can’t let the memory of him hold you back from trying new relationships.” Anna says, soothingly.

Castiel shakes his head, though he knows Anna won’t be able to see. “You don’t understand, Anna,” he begs, “it’s _Dean_.”

“Wait? Dean is your date tonight? How did that happen?”

“I don’t know,” Castiel sniffs, “I just know he’s here and, _God_ , Anna, I still love him as much as I did the night he left.”

“But, Castiel, why are you crying?” Anna asks, “Isn’t this a good thing? It’s all you’ve ever wanted. You guys could start again. He’s clearly single.” The hope and encouragement in Anna’s voice breaks Castiel’s heart even more.

“Because he won’t want to be with me now. He’s being kind and polite but we’re not even talking about what happened before. It’s like he wants to avoid it.” Castiel takes a deep breath to stop a fresh wave of tears.

“Cas, I’m sorry. At least you know now, you won’t have to wonder what could have been anymore. You can move on.”

Castiel nods to himself. “You’re right. It hurts but I know. I guess this is what I needed to finally move on.”

“Good. Now sort your face out and get back out there because you’ve been on the phone with me so long he’ll probably think you’ve got bowel issues.”

Castiel can’t help but huff a laugh at that. “Thanks for that, Anna. That really helped to calm my nerves.”

“What can I say? That’s what big sisters are for.” Castiel can hear her smile through the phone. “Now go and have one last date with Dean, get some closure and I’ll be waiting at yours with Mr Whiskers and pizza for when you get home. Okay?”

“Okay.”

“Good. Love you, Castiel.”

“Love you too, Anna. Thank you.”

Castiel ends the call and takes a deep breath before standing and unlocking the stall door. Luckily, there is no one in the rest of the bathroom who overheard that conversation.

Castiel checks himself out in the mirror, patting his face with some cold water to reduce the redness in his eyes from crying. Once he feels satisfied that he looks somewhat back to normal, he makes his way out the door and back to the table.

Honestly, Castiel has been gone so long he half expects Dean to have left.

But when he rounds the corner he spots Dean, still sat at the table, hunched over looking at his phone.

As Castiel approaches the table, Dean looks up, a kind smile on his face. “Hey, man. I’m glad you’re back, I was starting to worry a little there.”

Castiel manages a small smile in response and takes his seat again. “Thank you for your concern, Dean. But everything is fine.” He meets Dean’s eyes and tries his best to put on his most convincing smile.

But Dean clearly isn’t convinced. He frowns at Castiel and leans in a little further. “No, I know something’s wrong,” Dean whispers, searching Castiel’s eyes for the truth. “Come on, Cas. It’s me. Talk to me.”

Castiel feels his resolve start to crumble and his lip tremble. He bites his lip, hoping the cameras aren’t picking up on this moment. After a pause to console himself, he shakes his head. “It’s nothing. Truly.” He assures. “How’s your brother?” He asks, attempting to distract Dean.

Dean doesn’t look fully satisfied with Castiel’s response but he takes the bait. “Sam’s good. He’s in California now. He went to law school like he always wanted.” Dean beams with pride as he speaks. “Kid’s too smart for his own good if ya ask me.” Dean chuckles.

Castiel smiles softly. He never had the chance to meet Sam in the time he and Dean were together but Dean had talked about him enough that Castiel felt like he knew him. It makes him genuinely happy to hear that he got everything he worked hard for. Especially after everything their family went through.

“And how’s your father?”

The affectionate grin immediately leaves Dean’s face. “He, um, he died last year.”

Castiel feels his heart drop. “Dean, I-“

But Dean just shakes his head. “It’s okay, he wasn’t the same towards the end. Mom’s death really messed him up.”

“But still,” Castiel says, reaching a hand to cover Dean’s, “I know how much your family meant to you. I’m sorry that you had to go through that.” Castiel looks earnestly into Dean’s eyes.

“Thanks, Cas.”

A silence settles on them both for a few moments. Castiel is acutely aware of his hand still on Dean’s.

The silence is broken when Dean shakes his head and plasters a grin across his face. “Anyway, how’s Gabriel? Is he still getting up to his old tricks?”

And suddenly the moment between them is gone and Castiel is reminded of the Dean he first met back on their first day of college. The boy who hid his true feelings behind walls of humour and distraction. Castiel had worked so hard to break down those barriers.

Any hope of Dean still feeling the same after all these years is crushed. He doesn’t trust Castiel with his vulnerable moments anymore.

The rest of the date goes just as any other would. They argue a little over who is going to pay and they eventually just decide to split it.

However, unlike any other date Castiel has been on, once they leave their table they’re escorted to a back room to do their post-date interviews.

A producer comes up to Castiel and asks him to go into the room and sit down on one of the chairs. Then Dean will come in afterwards to make it look like they haven’t just been stood together awkwardly in the corridor.

The look of the room immediately makes Castiel’s heart rate pick up again. There’s just two chairs next to each other in front of a camera and another chair. Obviously, he’d been aware that there were cameras watching them during their meal but Castiel could pretend they weren’t there. Now the camera is right in front of them, glaring with its big black lens.

Soon enough, Dean walks in and takes the seat next to his. The producer follows in after and takes her seat next to the camera.

“So this is where we ask the obvious question,” the producer begins. “Would you like to see each other again?”

The question is met with silence.

Castiel feels brave and turns to face Dean. He looks into the eyes of the man he was once sure he’d spend the rest of his life with, and he asks himself the question.

_Do I want to see Dean again?_

Of course he does. But Dean doesn’t want it. He still hasn’t answered. And even if Dean says yes, Castiel is terrified of it all going wrong again. What if they’re just destined for failure? Dean is the love of his life, Castiel has no doubt about that. He wouldn’t be able to take it if it all fell apart again.

Dean must see the fear in Castiel’s eyes because he reaches out and puts a calming hand on Castiel’s. “Tell me what you’re thinking, Cas,” he whispers.

Seeing nothing but sincerity grace Dean’s green eyes, Castiel throws caution to the wind. He pretends the camera isn’t there and just lets go.

“I’m scared,” he admits.

“Scared of what, bab- _Cas_?” Dean asks and flushes at the slip.

Castiel feels his heart flutter at Dean almost calling him ‘babe’. It was always Dean’s favourite term of endearment for him.

Even if it was a slip that Dean regrets, it gives Castiel the final push of confidence to lay himself bare.

“I’m scared of putting my heart on the line again. I’m scared of telling you I still love you and you not saying it back. I’m scared that you will say it back and everything will still go wrong.” Castiel blinks back the tears building behind his eyes. He’s cried too much for one night. “I’ve had to leave you once before Dean. I don’t know if I can do it again.”

Dean lifts his hand to Castiel’s cheek. “So don’t.”

And with that he brings Castiel into a firm kiss that leaves nothing up to interpretation.

Castiel feels the life return to his body.

* * *

Anna hears her phone chime with a text. She halts her lavishing strokes on Mr Whiskers and reaches for the device. Frowning when she sees the message is from her brother, she quickly rushes to read to it, worried that he might be in trouble.

Instead she opens the message to find a picture. It takes a few seconds to load but once it does, she almost drops the phone.

It’s a picture of her brother wrapped up in the arms of none other than Dean Winchester. Dean’s older than when Anna had last seen him. But the smile on her brother’s face tells her all she needs to know. Castiel hasn’t smiled like that since he was in college. It makes her heartbeat with joy to finally see it return.

She’s so overwhelmed with happiness for her brother that she almost misses the caption on the photo.

_You should probably cancel that pizza. I’ll call you in the morning. Love you x_

Anna chuckles. But if Castiel thinks she’s going to cancel the pizza he’s got another thing coming. Her brother reuniting with his long-lost love is amazing, and she’s truly happy for him, but what is even more amazing is that she now gets a whole pizza to herself and endless kitty cuddles for a night. So who is the real winner?

She types out a response to Castiel’s message. Looking at the photo of him and Dean again, she can’t help but think that First Dates have just recorded their best episode yet.

**Author's Note:**

> Also posted on my [tumblr](https://dickspeightjrs.tumblr.com/). (Follow me?)
> 
> Comment and give a kudos if you liked?


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